Highly emissive organic solids with remarkably broad color tunability based on N,C-chelate, four-coordinate organoborons

Article abstract of DOI:10.1039/c5cc06351e

Molecular fluorophores based on N,C-chelate, four-coordinate organoborons exhibit tunable solid-state emission colors that cover the whole visible region from blue to red. The emission color can be tuned through the substituents on either quinolines or the boron center.

Full text of DOI:10.1039/c5cc06351e

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2015, DOI: 10.1039/C5CC06351E.
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Highly Emissive Organic Solids with Remarkably Broad Color
Tunability Based on N, C-Chelate Four-Coordinate Organoborons
Aslam C. Shaikh,a Dnyanesh S. Ranade,c Shridhar Thorat,b Arunava Maity,a Prasad P. Kulkarni,c
Rajesh G. Gonnade,b Parthapratim Munshi d and Nitin T. Patil*a
Received 00th January 20xx,
Accepted 00th January 20xx
DOI: 10.1039/x0xx00000x
www.rsc.org/
Abstract. Molecular fluorophores based on N,C-chelate four- initiated programme on identifying
a single type of boron-
coordinate organoborons exhibit tunable solid-state emission containing molecules capable of emitting light at different
colors that cover the whole visible region from blue to red. The wavelengths. In 2005, Wang and coworkers identified the
emission color can be tuned through the substituents on either luminescent N,N-chelate boron complexes whose solid state
quinolines or on boron center.
emission can be tuned from blue to red.11 In 2007, Yamaguchi and
coworkers reported full-color tunable emissive organic solids based
on 3-boryl-2,2’-bithiophene as a versatile core skeleton.12 You and
coworkers reported regiospecific N-heteroarylation of amidines for
full-color-tunable boron difluoride dyes with mechanochromic
luminescence.13 Zhang and Wang reported construction of strongly
emissive full-color tunable boron-containing materials by
functionalizing a boron-chelate-ring-fused π-conjugated core.14 Very
recently, Tanaka and Chujo showed that the emission color in boron
diiminates in the solid states can be modulated by the
substituents.15
Design and synthesis of luminescent organic materials is of
fundamental importance because of their potential application in
optoelectronic devices.1 Such luminescent organic materials can
also hold significant potential in the field of bio-imaging.2 Therefore,
the development of novel solid emitters3 which do not casue
aggregation-induced emission quenching4 has emerged a hot topic
of research. However, in most cases, the design is heavily relied on
mere functionalization of existing fluorophores. Considering the
demand of solid light emitters in material science and biology, there
is an urgent need for the identification novel core structures, with
full color-tunability, capable of emitting light in the aggregation
state.5
Inspired by the above reports, we designed a new class of full-
color tunable solid light emitters based on N,C-chelate four-
coordinate organoborons (Fig 1).16 It was envisaged that the
appropriate choice of substituent on either boron or on N,C-chelate
might allow us to achieve color-tunability in the solid state that
span the whole visible region. Herein, we report the successful
implementation of our studies.
In recent years, organoborons are considered as promising light
emitting materials owing to their intense luminescence and high
carrier mobility.6 In addition to their application in material
sciences, these compounds have potential applications in biology as
a
cell marker.7 The most potential examples of fluorescent
organoboron compounds are borondipyrromethene (BODIPY) dyes
and its analogues.8 However, in general, those dyes are emissive in
dilute solutions and they become non-emissive in the aggregate
state9 with some exceptions.10 Therefore, it is very challenging to
develop highly emissive solid organoborons; especially with a full-
color tunability using a single core skeleton by appropriate tuning of
the substituents.
N,C-chelate four-coordinate organoborons
N
N
Br
Br
B
B
X
R
R
Br
X
Al
R
X = Br or R
Modularand ScableSynthesis
RobustSynthetic Procedure
A Numberof DiversityPoints
Over the years, several research group across the world have
Synthesisof N,C-Chelate:Our Own Method (ref 17b)
ElectrophilicBorylation: Murakami'sMethod (ref 18)
a.Organic Chemistry Division, CSIR
- National Chemical Laboratory, Dr. Homi
Figure 1. General design of N,C-chelate four-coordinate
Bhabha Road, Pune - 411 008, India, E-mail: n.patil@ncl.res.in.
b.Center for Materials Characterization, CSIR - National Chemical Laboratory, Dr.
Homi Bhabha Road, Pune - 411 008, India.
organoborons
c. Bioprospecting Group, Agharkar Research Institute, Pune - 411 004, India.
d.Department of Chemistry, School of Natural Sciences, Shiv Nadar University, UP
203207, India
A
series requisite N,C-chelate four-coordinate organoborons
were synthesized in a stepwise manner as outlined in Scheme 1.
The pre-requisite 2-substituted quinolines were prepared by the
method developed by us17 with slight modifications. Treatment of
2-aminobenzaldehydes with appropriate alkynes under the catalysis
Electronic Supplementary Information (ESI) available: [details of any
supplementary information available should be included here]. See
DOI: 10.1039/x0xx00000x
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with Au(I) and p-anisidine provided the products 1-6 in yields
ranging from 80-95%. Following the procedure reported by
Murakami,18 the targeted quinoline−borane complexes were
synthesized from 2-arylquinolines through an electrophilic aromatic
borylation reaction with BBr3. The intermediate 2-(2-
dibromoborylaryl) pyridines were stable enough to be handled in
air and served as the synthetic platform for variously substituted
quinoline−borane complexes. All the structures were fully
characterized by spectral and analytical methods.19 All of the N, C-
chelate four-coordinate organoborons produced are stable in air
and water, and can be purified by column chromatography on silica
gel. These compounds have a high thermal stability; for example,
the decomposition temperatures for a 5% weight loss (Td5) of 4a
and 5a are 335 °C and 298 °C, respectively.19
Figure 2. (a) Emission spectra (excited with longest absorption
maxima) in CH2Cl2 and (b) Emission spectra in the solid state
(powder) and (c) photographic images (excited at 365 nm using a
UV lamp) of solution and solid compounds.
All complexes showed strong broad solid-state absorption in the
UV-visible region between 397 - 496 nm and intense solid-state
fluorescence emission between 491 - 670 nm (Fig 2b). The
fluorescence of the solid samples with emission peaks at 491 nm
(greenish blue for 1a) and 670 nm (deep red for 6e) also covered a
wide range from blue to deep red (Fig 2c). The emission maxima of
complexes 1a – 6e in solid state shows blue and red shifted
compared with those of solution state which reflected
crystallochromy effects. The wavelength of the emission maximum
(λem) of 6d (R = phenyl) and 6e (R = Br) is red shifted by 44 nm and
130 nm than that of 6a (R = Me) respectively and for 6a (R = Me),
6b (R = Ethyl) and 6c (R = n-octyl) is almost similar which indicates
the effect of substituent present at boron center with respect to
quinoline π-framework. To evaluate the substitution effect on the
photo-physical properties, the absorption and emission spectra of
diphenylamine- and carbazole- substituted boron complexes 2a and
4a in CH2Cl2 and solid state were compared. These two complexes
showed completely different absorption and emission properties
merely due to the subtle difference in substitution, despite their
structural similarity. As depicted in Fig. 2, the carbazole-substituted
boron complex 4a is greenish-blue emissive with an absorption
band centred at 387 nm and an emission band which peaked at 497
Scheme 1. Synthesis of N,C-chelate four-coordinate organoborons
The organoborons 1a – 6e showed intense fluorescence in
solution and in the solid state. The photophysical data of
complexes 1a – 6e recorded in CH2Cl2 and solid state (Table 1). All
of the complexes exhibited a broad absorption band between 387 -
491 nm attributable to the electronic transition originating from the
π-molecular orbitals. All the fluorophores exhibited intense
emission in CH2Cl2 solutions when excited at their absorption
maxima. The emission profiles of these complexes in solution,
having emission bands that peaked at 466 nm (1a, blue) to 637 nm
(2c, red), covered a wide range from blue to red, reflecting that the
substituent at the two position of quinolines was indeed effective in
tuning the emission color of this type of N,C-chelate four-
coordinate organoborons (Fig 2c). The absolute fluorescence
quantum yields in solutions were measured using an integrating
sphere method. The N,C- chelate four-coordinate organoboron
wherein the methyl groups exist on boron center showed good
quantum yield (Фf 0.81 for 3a) as compared to those with bromo
substituents (Фf 0.03 for 2c).
2 | J. Name., 2012, 00, 1-3
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nm. Diphenylamine-substituted boron complex 2a is greenish the experimental UV-vis values (Table 2).19 In the case of organo-
yellow fluorescent with the longest absorption maximum of 433 nm borons 3a, 4a, 5a the theoretical values are over estimated by
and emission band centred at 546 nm, exhibiting 46 and 49 nm red 17.5%, 21.1% and 3.52% respectively, in compared to the
shifts for absorption and emission maxima compared to 4a. experimental UV-Vis values. In addition, the dipole moment values
Similarly in solid state 4a shows emission at 491 nm and 2a shows are found to be correlate well with the planarity of the molecules.
at 525 nm. According to density functional theory (DFT)
calculations, the electron-donating group substituted at the para Table 2. Comparison of UV absorption with the HOMO-LUMO gap
position significantly pushed the HOMO level up, hence narrowing calculated based on optimized crystal geometries
the energy gap of the boron complex.19 In view of these
comparisons, it is clear that only the slight difference in the
chemical structure, results in a significant difference in the photo
physical properties of complexes. All the solid samples are highly
emissive and their quantum yields were determined using an
integrating sphere. The compound 4a shows highest quantum yield
(Фf 0.41) in solid state powder form with respect to other
complexes. It should be noted that the N,C-chelate four-coordinate
organoborons also showed positive solvatochromic behaviour as
emission wavelengths were found to be red shifted with increase in
solvent polarity.19
Table 1. Photophysical data
f e
em(nm)c
d
(cm-1
)
abs (nm)a
CH2Cl2 solidb
Stokes
CH2Cl2
f
Comp
f
CH2Cl2
solid
CH2Cl2 solid
(ns)
solid
1a
2a
2b
2c
406
433
434
491
405
466
459
502
466
546
548
637
491
525
524
642
3170
4774
4791
4661
4323
2412
2696
4343
0.58
0.56
0.60
0.03
0.12
0.18
0.13
0.14
5.2
6.4
6.0
2.1
3a
3b
4a
4b
4c
418
463
387
387
435
415
470
397
401
434
491
543
497
492
600
584
654
491
497
631
3553
3180
5709
5504
6313
6966
5980
4820
4809
7192
0.81
0.60
0.71
0.67
0.09
0.19
0.11
0.41
0.38
0.04
4.0
4.8
6.2
6.1
3.2
5a
6a
6b
6c
6d
405
433
432
431
429
435
439
459
463
531
531
532
507
540
542
534
3091
4257
4257
4403
3590
4461
4319
3053
0.78
0.50
0.59
0.53
0.13
0.36
0.32
0.21
5.5
6.6
6.2
6.9
452
487
473
496
549
589
584
670
3905
3552
4016
5234
0.43
0.14
0.05
0.15
6.9
2.5
6e
aThe maximum absorption bands more than 300 nm.bSpincoated film prepared from a
CH2Cl2 solution. cExcited at the longest maximum absorption band in CH2Cl2 and powder
form. dStokes shift = The difference between higher energy absorption maximum and the
emission maximum. eAbsolute quantum yields were measured using an integrating sphere
The single crystal X-ray structure provides better understanding
about the PL properties of the luminogens. The molecular packing
patterns in the crystals of 2a (CCDC 1408898), 3a (CCDC 1408899),
4a (CCDC 1408900) is displayed in Figure 3 and that of 5a (CCDC
1408901) and 6b (CCDC 1408902) are provided in the Supporting
Information. Molecules of these compounds are closely packed in
their respective crystals via face-to-face π···π stacking interactions
with inter centroid distances ranging from 3.636(5) Å to 3.974(5) Å
involving either quinoline-quinoline rings or phenyl-quinoline rings.
All these hydrophobic forces work collectively to restrict the
intramolecular rotation process and hence promote the radiative
relaxation of the excited state, causing the molecules to exhibit
fluorescence strongly. The luminescence properties were also
rationalized by the DFT level of theory using B3LYP functional and 6-
311G** basis set. The HOMO-LUMO gaps estimated from
theoretical calculations were found to be in a good agreement with
Figure 3. Single crystal packing of 2a (a), 3a (b) and 4a (c)
Further, the feasibility of luminogens for biological imaging was
studied by performing confocal imaging in MCF-7 cancer cell line
which suggests that these N,C-chelate four-coordinate
organoborons can successfully be exploited for in vitro bio-
imaging.19
In summary, a series of highly emissive molecular solids based on
N,C-chelate four-coordinate organoborons have been designed and
synthesized. The results show the versatility of the 2-arylquinoline
chelates for attaining an intense emission, with the maxima ranging
over the whole visible region. The fluorophores have successfully
marked MCF cells exhibiting their future potential as useful
bioimaging fluorescence probes. Excellent photophysical properties
combined with their thermal stability and DFT studies indicates that
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this class of compounds could have potential application in
optoelectronic devices as well.
Generous financial supports by the DST-New Delhi (No.
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of SPM research fellowship. We also thank Dr. P. Thilagar and Samir
K. Sarkar, IISc, Bangalore for helping us in the mesurement of
quantum yields in the solid state. We thank Dr. Amitava Das, CSIR-
NCL for helping us in the determination of photo-physical
properties. Special thanks to Dr. K. Krishnamoorthy for the
measurement of UV-vis absorption in spincoated film.
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